GET FESTIVE: BEST FESTIVALS IN STAYPINEAPPLE CITIES
Photo by Gpointstudio via Canva
From the eclectic arts and indie music at Seattle's beloved Bumbershoot Arts & Music Festival at the Seattle Center, just a short walk from The Maxwell Hotel, to the soulful sounds of the Chicago Jazz Festival in Millennium Park, just a quick stroll from Staypineapple Chicago, there's plenty of festival fun waiting in our cities. Book your getaway, bring your appetite for adventure and make memories that last long after the festivities fade!
SEATTLE, WA
Blue Angels at Seafair Festival | Photo by Marco Bicca via Unsplash
Seattle International Film Festival
When: May 15-25, 2025
Where: Venues across Seattle including:
- SIFF Cinema Uptown (10-min walk from The Maxwell Hotel)
- SIFF Cinema Downtown (3-min walk from Hotel FIVE)
Held across multiple venues, the festival showcases over 100 independent and international films. When you come to celebrate the magic of film, save on your stay with promo code FESTIVAL and make your SIFF experience even more cinematic!
When: July 19, 2025
Where: University District (participating shops within short walking distance from Watertown Hotel & University Inn)
Celebrate the U District as the bubble tea capital of the Northwest, featuring tasty flavors and bubble tea-inspired treats in the heart of boba culture.
When: August 1-3, 2025
Where: Genesee Park (20-min drive from The Maxwell Hotel and Hotel FIVE)
An annual Seattle tradition featuring Blue Angels air shows, hydroplane races, car shows, live music, food and family fun.
When: August 1-3, 2025
Where: Genesee Park (20-min drive from The Maxwell Hotel and Hotel FIVE)
An annual Seattle tradition featuring Blue Angels air shows, hydroplane races, car shows, live music, food and family fun.
Bumbershoot Arts & Music Festival
When: August 30-31, 2025
Where: Seattle Center (2-min walk from The Maxwell Hotel)
Over Labor Day weekend, the festival brings top music acts, immersive art, local food and creative experiences to Seattle Center.
PORTLAND, OR
Portland Waterfront Blues Festival | Photo by NASHCO Photo via Travel Portland
Portland Rose Festival
When: May 23-June 8, 2025
Where: Tom McCall Waterfront Park (across the street from Hotel Rose)
During the festival, the park hosts CityFair – a lively carnival with rides, live music, food and vendors. The Grand Floral and Starlight Parade routes run nearby, offering easy access to enjoy the festivities.
Waterfront Blues Festival
When: July 4-5, 2025
Where: Tom McCall Waterfront Park (across the street from Hotel Rose)
A fun summer event featuring incredible live music, delicious food and drinks, and a spectacular Fourth of July fireworks show over the Willamette River.
Portland Craft Beer Festival
When: July 4-6, 2025
Where: Elizabeth Caruthers Park (7-min drive from Hotel Rose)
A big outdoor party showcasing the widest selection of local beers, ciders, and wine-based cocktails – all crafted in Portland.
Project Pabst
When: July 26-27, 2025
Where: Tom McCall Waterfront Park (across the street from Hotel Rose)
A 21+ music festival created by the famous Pabst Brewing Company, features an exciting mix of well-known and emerging artists.